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Name |
6-Mercaptopurine |
EINECS | 200-037-4 |
CAS No. | 50-44-2 | Density | 1.82 g/cm3 |
PSA | 89.45000 | LogP | 1.01550 |
Solubility | 124mg/L(25 oC) | Melting Point |
241-244 °C |
Formula | C5H4N4S | Boiling Point | 471.018 °C at 760 mmHg |
Molecular Weight | 152.18 | Flash Point | 238.663 °C |
Transport Information | N/A | Appearance | yellowish-greenish solid |
Safety | Risk Codes | N/A | |
Molecular Structure | Hazard Symbols | N/A | |
Synonyms |
6-Mercaptopurinum;6-Mercaptopurine, >99%;NSC-755;Mercaleukin;Purine-6-thiol, monohydrate;6-mercapto-;9H-Purin-6-yl hydrosulfide;6-Thioxopurine;U-4748;Puri-Nethol;1,7-Dihydro-6H-purine-6-thione;6-Thiopurine;6H-Purine-6-thione, 1,7-dihydro-;7-Mercapto-1,3,4,6-tetrazaindene;Hypoxanthine, thio-;6-Purinethiol;Mercaleukim;7H-purine-6-thiol; |
Article Data | 21 |
Conditions | Yield |
---|---|
With potassium hydrosulfide und Erwaermen des Reaktionsprodukts mit einem Gemisch von Jod, konz.HI und rotem Phosphor; |
[1,3]thiazolo[5,4-d]pyrimidin-7-amine
formamide
6H-purine-6-thione
Conditions | Yield |
---|---|
at 190℃; | |
at 190℃; |
6-amino-5-formylamino-3H-pyrimidin-4-one
6H-purine-6-thione
Conditions | Yield |
---|---|
With pyridine; tetraphosphorus decasulfide | |
With tetraphosphorus decasulfide; tetralin |
N-(4-amino-6-thioxo-1,6-dihydro-pyrimidin-5-yl)-formamide
6H-purine-6-thione
Conditions | Yield |
---|---|
With formamide at 200℃; |
5-Aminoimidazole-4-thioamide
formamide
6H-purine-6-thione
Conditions | Yield |
---|---|
at 200℃; |
Conditions | Yield |
---|---|
With ethanol |
Conditions | Yield |
---|---|
With tetraphosphorus decasulfide; tetralin | |
With pyridine; tetraphosphorus decasulfide | |
Multi-step reaction with 2 steps 1: N,N-dimethyl-aniline; POCl3 2: ethanol View Scheme |
S6-(N-methyl-N-methoxycarbonyl)aminomethyl-6-mercaptopurine
6H-purine-6-thione
Conditions | Yield |
---|---|
With phosphate buffer; water at 32℃; Rate constant; Mechanism; pH 7.1; |
S6-(N-methyl-N-ethoxycarbonyl)aminomethyl-6-mercaptopurine
6H-purine-6-thione
Conditions | Yield |
---|---|
With phosphate buffer; water at 32℃; Rate constant; pH 7.1; |
S6-(N-ethyl-N-methoxycarbonyl)aminomethyl-6-mercaptopurine
6H-purine-6-thione
Conditions | Yield |
---|---|
With phosphate buffer; water at 32℃; Rate constant; pH 7.1; |
IARC Cancer Review: Group 3 IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 ,1987,p. 240.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Inadequate Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 26 ,1981,p. 249.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Human Inadequate Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 26 ,1981,p. 249.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . NCI Carcinogenesis Studies (ipr); Equivocal Evidence: rat CANCAR Cancer. 40 (1977),1935. ; (ipr); Clear Evidence: mouse CANCAR Cancer. 40 (1977),1935. . EPA Genetic Toxicology Program.
6-Mercaptopurine, with the CAS NO.50-44-2, is an immunosuppressive drug. It has the Synonyms of LEUKERIN; 1,7-Dihydro-6H-purine-6-thione; 7H-PURINE-6-THIOL; 7-mercapto-1,3,4,6-tetrazaindene; 6-MERCAPTOPURINE; 6-PURINETHIOL; 6-THIOPURINE; 6-thioxopurine. It is used to treat leukemia, pediatric non-Hodgkin's lymphoma,[citation needed] polycythemia vera, psoriatic arthritis, and inflammatory bowel disease. 6-Mercaptopurine can be obtained by the reaction of seq xanthine with phosphorus pentasulfide.
Physical properties about 6-Mercaptopurine are: (1)ACD/LogP: -0.632; (2)ACD/LogD (pH 5.5): -0.64; (3)ACD/LogD (pH 7.4): -0.82; (4)ACD/BCF (pH 5.5): 1.00; (5)ACD/BCF (pH 7.4): 1.00; (6)ACD/KOC (pH 5.5): 10.71; (7)ACD/KOC (pH 7.4): 6.95; (8)#H bond acceptors: 4; (9)#H bond donors: 2; (10)Index of Refraction:1.941; (11)Molar Refractivity: 40.028 cm3; (12)Molar Volume: 83.36 cm3; (13)Polarizability:15.868 10-24cm3; (14)Surface Tension: 75.4020004272461 dyne/cm; (15)Density: 1.826 g/cm3; (16)Flash Point: 255.372 °C; (17)Enthalpy of Vaporization: 76.687 kJ/mol; (18)Boiling Point: 498.646 °C at 760 mmHg
You can still convert the following datas into molecular structure:
(1)InChI=1S/C5H4N4S/c10-5-3-4(7-1-6-3)8-2-9-5/h1-2H,(H2,6,7,8,9,10);
(2)InChIKey=GLVAUDGFNGKCSF-UHFFFAOYSA-N;
(3)Smilesc12c(nc[nH]c1=S)nc[nH]2
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
hamster | LD50 | intraperitoneal | 364mg/kg (364mg/kg) | Archives of Toxicology. Vol. 32, Pg. 1, 1974. | |
man | TDLo | oral | 40mg/kg/1W-I (40mg/kg) | SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" | Archives of Dermatology. Vol. 122, Pg. 1413, 1986. |
mouse | LD50 | intraperitoneal | 80mg/kg (80mg/kg) | Cancer Research. Vol. 42, Pg. 122, 1982. | |
mouse | LD50 | intravenous | 80mg/kg (80mg/kg) | Cancer Research. Vol. 42, Pg. 122, 1982. | |
mouse | LD50 | oral | 260mg/kg (260mg/kg) | Cesko-Slovenska Farmacie. Vol. 14, Pg. 389, 1965. | |
mouse | LD50 | subcutaneous | 100mg/kg (100mg/kg) | IMMUNOLOGICAL INCLUDING ALLERGIC: DECREASE IN HUMORAL IMMUNE RESPONSE | Journal of Medicinal Chemistry. Vol. 18, Pg. 320, 1975. |
rat | LD50 | intraperitoneal | 159mg/kg (159mg/kg) | Acta Poloniae Pharmaceutica. For English translation, see APPFAR. Vol. 41, Pg. 571, 1984. | |
rat | LD50 | intravenous | 250mg/kg (250mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 20, Pg. 1467, 1970. | |
rat | LD50 | oral | 277mg/kg (277mg/kg) | Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 15, Pg. 1037, 1973. | |
rat | LD50 | parenteral | 250mg/kg (250mg/kg) | Recent Results in Cancer Research. Vol. 52, Pg. 76, 1975. | |
rat | LD50 | subcutaneous | 90mg/kg (90mg/kg) | Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 15, Pg. 1037, 1973. |